Secondary (chemistry)

Secondary is a term used in organic chemistry to classify various types of compounds (e. g. alcohols, alkyl halides, amines) or reactive intermediates (e. g. alkyl radicals, carbocations). An atom is considered secondary if it has two 'R' Groups attached to it.[1] An 'R' group is a carbon containing group such as a methyl (). A secondary compound is most often classified on an alpha carbon (middle carbon) or a nitrogen. The word secondary comes from the root word 'second' which means two.

Red highlighted central atoms in various groups of chemical compounds.

Secondary central atoms compared with primary, tertiary and quaternary central atoms.

primary secondary tertiary quaternary
Carbon atom in an alkane


This nomenclature can be used in many cases and further used to explain relative reactivity. The reactivity of molecules varies with respect to the attached atoms. Thus, a primary, secondary, tertiary and quaternary molecule of the same function group will have different reactivities.

Secondary alcohols

Secondary alcohols have the formula RCH(OH)R' where R and R' are organyl.[2]

Primary Secondary Tertiary Quaternary
Alcohol does not exist

Secondary amines

A secondary amine has the formula RR'NH where R and R' are organyl.

Primary Secondary Tertiary Quaternary
Amine

Secondary amides

Secondary amides have the formula RC(O)NHR' where R can be H or organyl and R' is organyl.[3] which is the loss of the single proton bonded to the middle nitrogen.

Primary Secondary Tertiary Quaternary
Amide does not exist

Secondary phosphines

Secondary phosphines have two 'R' groups attached to a phosphorus atom and again, a P-H bond.[4]

Primary Secondary Tertiary Quaternary
Phosphine

Further uses

"Secondary" is a general term used in chemistry that can be applied to many molecules, even more than the ones listed here; the principles seen in these examples can be further applied to other functional group containing molecules. The ones shown above are common molecules seen in many organic reactions. By classifying a molecule as secondary it then be compared with a molecule of primary or tertiary nature to determine the relative reactivity.   

See also

References
  1. Ashenhurst, James (2010-06-16). "Primary, Secondary, Tertiary, Quaternary In Organic Chemistry". Master Organic Chemistry. Retrieved 2022-10-06.
  2. "alcohol - Structure and classification of alcohols | Britannica". www.britannica.com. Retrieved 2022-10-18.
  3. "Secondary Amide - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2022-10-24.
  4. Nell, Bryan P.; Tyler, David R. (2014-11-01). "Synthesis, reactivity, and coordination chemistry of secondary phosphines". Coordination Chemistry Reviews. 279: 23–42. doi:10.1016/j.ccr.2014.07.002. ISSN 0010-8545.
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